US8492511B2 - Process for the preparation of crosslinked nitroxide polymers - Google Patents
Process for the preparation of crosslinked nitroxide polymers Download PDFInfo
- Publication number
- US8492511B2 US8492511B2 US12/296,330 US29633007A US8492511B2 US 8492511 B2 US8492511 B2 US 8492511B2 US 29633007 A US29633007 A US 29633007A US 8492511 B2 US8492511 B2 US 8492511B2
- Authority
- US
- United States
- Prior art keywords
- transition metal
- process according
- bis
- chloro
- bromo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 0 [3*]N(C)C Chemical compound [3*]N(C)C 0.000 description 13
- VNTMVKHIVLQJLS-UHFFFAOYSA-N CC1CC(C)(C)N([O])C(C)(C)C1.CC1CC(C)(C)N([O])C2(C1)CC(C)(C)N([O])C(C)(C)C2.CN(C1CC(C)(C)N(C)C(C)(C)C1)C1CC(C)(C)N([O])C(C)(C)C1 Chemical compound CC1CC(C)(C)N([O])C(C)(C)C1.CC1CC(C)(C)N([O])C2(C1)CC(C)(C)N([O])C(C)(C)C2.CN(C1CC(C)(C)N(C)C(C)(C)C1)C1CC(C)(C)N([O])C(C)(C)C1 VNTMVKHIVLQJLS-UHFFFAOYSA-N 0.000 description 2
- LHPDAPVJSKDGCA-UHFFFAOYSA-N CCN([O])CC Chemical compound CCN([O])CC LHPDAPVJSKDGCA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
Description
wherein
- Ln is a n valent spacer group or a repeating unit connecting the nitroxide groups;
- n is a number from 3 to 50 000 and wherein
- the molar ratio of the bis or polynitroxide compound of formula (A) or (B) to the bis-functional or polyfunctional halogen compound is equal or greater than 5:1.
(F) wherein G1 and G2 independently represent a tertiary carbon atom to which unsubstituted C1-C18alkyl or phenyl; or
- C1-C18alkyl or phenyl substituted with CN, OH, COC1-C18alkyl, CO-phenyl, COOC1-C18alkyl, OC1-C18alkyl, NO2, NHC1-C18alkyl or N(C1-C18)2alkyl are bonded; or one of
- G1 and G2 is a secondary carbon atom to which a group —P(O)(OR22)2 is bonded and the other is as defined above; or
- G1 and G2 together with the nitrogen atom to which they are bonded form a 5 to 8 membered heterocyclic ring or a polycyclic or spirocyclic 5 to 20 membered heterocyclic ring system, which is substituted with 4 C1-C4alkyl groups or 2 C5-C12 spirocycloalkyl groups in ortho position to the nitrogen atom and which may be further substituted with one or more C1-C18alkyl, C1-C18alkoxy or ═O groups; and
- which may be interrupted by a further oxygen or nitrogen atom;
- L1 and L2 are linking groups which are for example R101—Y or R102—C(O)—Y— where Y is attached to G1 and/or G2; C1-C25alkylene, C2-C25alkylene interrupted by —O—, —S—, —SO—, —SO2—,
- wherein R101 is C1-C18alkylene, R102 is a direct bond or C1-C18alkylene, R103 and R104 are independently hydrogen or C1-C18alkyl and R109 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C3-C18alkinyl, phenyl, C7-C9phenylalkyl, which all may be unsubstituted or substituted by one or more hydroxy, halogen or C1-C4alkoxy groups.
is, for example, CH3—O—CH2CH2—, CH3—S—CH2CH2—, CH3—N(CH3)—CH2CH2—, CH3—O—CH2CH2—O—CH2CH2—, CH3—(O—CH2CH2—)2O—CH2CH2—, CH3—(O—CH2CH2—)3O—CH2CH2— or CH3—(O—CH2CH2—)4O—CH2CH2—.
- R12 is H, C1-C12alkyl, C5-C12cycloalkyl or aryl or a group —(CH2)q-NR10R11;
- m, p and q are numbers from 1-4;
- n is a number from 0 to 4; or
- the ligand is a bicyclic or polycyclic heteroaliphatic ring.
- R15, and R16 are H, C1-C12alkyl, C6-C10aryl, C5-C12cycloalkyl;
- aryl is phenyl, naphthyl or biphenyl;
- Y is O or NR15;
- R17 is a 2-10 valent organic or inorganic residue
- r is a number from 2 to 10
- s is a number from 2 to 6 and
- X is Cl or Br.
- Bromo-acetic acid 2-(2-bromo-acetoxy)-ethyl ester,
- 2-Bromo-propionic acid 2-(2-bromo-propionyloxy)-ethyl ester,
- Bromo-acetic acid 3-(2-bromo-acetoxy)-propyl ester,
- 2-Bromo-propionic acid 3-(2-bromo-propionyloxy)-propyl ester,
- Bromo-acetic acid 4-(2-bromo-acetoxy)-butyl ester,
- 2-Bromo-propionic acid 4-(2-bromo-propionyloxy)-butyl ester,
- Bromo-acetic acid 5-(2-bromo-acetoxy)-pentyl ester,
- 2-Bromo-propionic acid 5-(2-bromo-propionyloxy)-pentyl ester,
- Bromo-acetic acid 6-(2-bromo-acetoxy)-hexyl ester,
- 2-Bromo-propionic acid 6-(2-bromo-propionyloxy)-hexyl ester,
- Bromo-acetic acid 12-(2-bromo-acetoxy)-dodecyl ester,
- 2-Bromo-propionic acid 12-(2-bromo-propionyloxy)-dodecyl ester,
- Chloro-acetic acid 2-(2-chloro-acetoxy)-ethyl ester,
- 2-Chloro-propionic acid 2-(2-chloro-propionyloxy)-ethyl ester,
- Chloro-acetic acid 3-(2-chloro-acetoxy)-propyl ester,
- 2-Chloro-propionic acid 3-(2-chloro-propionyloxy)-propyl ester,
- Chloro-acetic acid 4-(2-chloro-acetoxy)-butyl ester,
- 2-Chloro-propionic acid 4-(2-chloro-propionyloxy)-butyl ester,
- Chloro-acetic acid 5-(2-chloro-acetoxy)-pentyl ester,
- 2-Chloro-propionic acid 5-(2-chloro-propionyloxy)-pentyl ester,
- Chloro-acetic acid 6-(2-chloro-acetoxy)-hexyl ester,
- 2-Chloro-propionic acid 6-(2-chloro-propionyloxy)-hexyl ester,
- Chloro-acetic acid 12-(2-chloro-acetoxy)-dodecyl ester,
- 2-Chloro-propionic acid 12-(2-chloro-propionyloxy)-dodecyl ester,
- Bromo-acetic acid 2,3-bis-(2-bromo-acetoxy)-propyl ester,
- 2-Bromo-propionic acid 2,3-bis-(2-bromo-propionyloxy)-propyl ester,
- Bromo-acetic acid 2,3,4-tris-(2-bromo-acetoxy)-butyl ester,
- 2-Bromo-propionic acid 2,3,4-tris-(2-bromo-propionyloxy)-butyl ester,
- Bromo-acetic acid 2,3,4,5-tetrakis-(2-bromo-acetoxy)-pentyl ester,
- 2-Bromo-propionic acid 2,3,4,5-tetrakis-(2-bromo-propionyloxy)-pentyl ester,
- Bromo-acetic acid 2,3,4,5,6-pentakis-(2-bromo-acetoxy)-hexyl ester,
- 2-Bromo-propionic acid 2,3,4,5,6-pentakis-(2-bromo-propionyloxy)-hexyl ester,
- Chloro-acetic acid 2,3-bis-(2-chloro-acetoxy)-propyl ester,
- 2-Chloro-propionic acid 2,3-bis-(2-chloro-propionyloxy)-propyl ester,
- Chloro-acetic acid 2,3,4-tris-(2-chloro-acetoxy)-butyl ester,
- 2-Chloro-propionic acid 2,3,4-tris-(2-chloro-propionyloxy)-butyl ester,
- Chloro-acetic acid 2,3,4,5-tetrakis-(2-chloro-acetoxy)-pentyl ester,
- 2-Chloro-propionic acid 2,3,4,5-tetrakis-(2-chloro-propionyloxy)-pentyl ester,
- Chloro-acetic acid 2,3,4,5,6-pentakis-(2-chloro-acetoxy)-hexyl ester,
- 2-Chloro-propionic acid 2,3,4,5,6-pentakis-(2-chloro-propionyloxy)-hexyl ester,
- Bromo-acetic acid 3-(2-bromo-acetoxy)-2,2-bis-(2-bromo-acetoxymethyl)-propyl ester,
- 2-Bromo-propionic acid 3-(2-bromo-propionyloxy)-2,2-bis-(2-bromo-propionyloxymethyl)-propyl ester,
- Chloro-acetic acid 3-(2-chloro-acetoxy)-2,2-bis-(2-chloro-acetoxymethyl)-propyl ester, 2-Chloro-propionic acid 3-(2-chloro-propionyloxy)-2,2-bis-(2-chloro-propionyloxymethyl)-propyl ester,
- 1,2-Bis-bromomethyl-benzene,
- 1,3-Bis-bromomethyl-benzene,
- 1,4-Bis-bromomethyl-benzene,
- 1,3,5-Tris-bromomethyl-benzene,
- 1,2,3,4,5,6-Hexakis-bromomethyl-benzene,
- 2-Bromo-N-[4-(2-bromo-propionylamino)-phenyl]-propionamide,
- 2-Bromo-propionic acid 4-(2-bromo-propionyloxy)-phenyl ester,
- 2-Bromo-N-[2-(2-bromo-propionylamino)-ethyl]-propionamide,
- 2-Bromo-propionic acid 2-(2-bromo-propionylamino)-ethyl ester,
- 2-Bromo-N-[6-(2-bromo-propionylamino)-hexyl]-propionamide,
- 1,2-Bis-chloromethyl-benzene,
- 1,3-Bis-chloromethyl-benzene,
- 1,4-Bis-chloromethyl-benzene,
- 1,3,5-Tris-chloromethyl-benzene,
- 1,2,3,4,5,6-Hexakis-chloromethyl-benzene,
- 2-Chloro-N-[4-(2-chloro-propionylamino)-phenyl]propionamide,
- 2-Chloro-propionic acid 4-(2-chloro-propionyloxy)-phenyl ester,
- 2-Chloro-N-[2-(2-chloro-propionylamino)-ethyl]-propionamide,
- 2-Chloro-propionic acid 2-(2-chloro-propionylamino)-ethyl ester and
- 2-Chloro-N-[6-(2-chloro-propionylamino)-hexyl]-propionamide.
- R200 is H or C1-C4alkyl
- Y is O or NR201 wherein R201 is H or C1-C18alky;
- Q is a nitroxide radical selected from the group of formulae (Ia) to (Ip) and
- n is a number from 10 to 50 000.
Claims (15)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06112360 | 2006-04-07 | ||
EP06112360 | 2006-04-07 | ||
EP06112360.0 | 2006-04-07 | ||
PCT/EP2007/052973 WO2007115939A1 (en) | 2006-04-07 | 2007-03-28 | Process for the preparation of crosslinked nitroxide polymers |
Publications (2)
Publication Number | Publication Date |
---|---|
US20100240858A1 US20100240858A1 (en) | 2010-09-23 |
US8492511B2 true US8492511B2 (en) | 2013-07-23 |
Family
ID=37057248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/296,330 Expired - Fee Related US8492511B2 (en) | 2006-04-07 | 2007-03-28 | Process for the preparation of crosslinked nitroxide polymers |
Country Status (6)
Country | Link |
---|---|
US (1) | US8492511B2 (en) |
EP (1) | EP2013240B1 (en) |
JP (1) | JP5364947B2 (en) |
CN (1) | CN101490100B (en) |
TW (1) | TWI472542B (en) |
WO (1) | WO2007115939A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1836201B2 (en) | 2004-12-20 | 2013-09-04 | Genentech, Inc. | Pyrrolidine inhibitors of iap |
US20090274947A1 (en) * | 2006-09-12 | 2009-11-05 | Peter Nesvadba | Imidazolidinone nitroxides as electrode materials for energy storage devices |
NZ590550A (en) | 2008-08-02 | 2013-05-31 | Genentech Inc | Inhibitors of Apoptosis (IAP) for treating cancer |
JP5366854B2 (en) * | 2009-02-19 | 2013-12-11 | 三菱レイヨン株式会社 | (Meth) acrylic acid ester |
JP2011126969A (en) * | 2009-12-16 | 2011-06-30 | Sumitomo Seika Chem Co Ltd | N,n-bis-(2,2,6,6-tetramethylpiperidin-n-oxyl-4-yl)-amine-(meth)acrylamide compound and n,n-bis-(2,2,6,6-tetramethylpiperidin-n-oxyl-4-yl)-amine-(meth)acrylamide compound crosslinked polymer |
JP5555485B2 (en) * | 2009-12-16 | 2014-07-23 | 住友精化株式会社 | N, N-bis- (2,2,6,6-tetramethyl-piperidin-4-yl) -amine- (meth) acrylamide and N, N-bis- (2,2,6,6-tetramethyl- Piperidine-N-oxyl-4-yl) -amine- (meth) acrylamide compound cross-linked polymer |
ES2770105T3 (en) | 2016-06-02 | 2020-06-30 | Evonik Operations Gmbh | Procedure for the production of an electrode material |
ES2795276T3 (en) | 2016-09-06 | 2020-11-23 | Evonik Operations Gmbh | Procedure for enhanced oxidation of secondary amino groups |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001083672A (en) | 1999-09-08 | 2001-03-30 | Fuji Photo Film Co Ltd | Production of polymer and dye fixing element containing same |
WO2004026915A1 (en) | 2002-09-23 | 2004-04-01 | Ciba Specialty Chemicals Holding Inc. | Polymeric alkoxyamines prepared by atom transfer radical addition (atra) |
WO2005116092A1 (en) | 2004-05-31 | 2005-12-08 | Sumitomo Seika Chemicals Co., Ltd. | Method for producing crosslinked poly(meth)acrylate compound |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2791979B1 (en) * | 1999-04-08 | 2003-05-16 | Atochem Elf Sa | PROCESS FOR THE PREPARATION OF ALCOXYAMINES FROM NITROXIDES |
-
2007
- 2007-03-28 JP JP2009503541A patent/JP5364947B2/en not_active Expired - Fee Related
- 2007-03-28 EP EP07727445.4A patent/EP2013240B1/en not_active Not-in-force
- 2007-03-28 WO PCT/EP2007/052973 patent/WO2007115939A1/en active Application Filing
- 2007-03-28 US US12/296,330 patent/US8492511B2/en not_active Expired - Fee Related
- 2007-03-28 CN CN200780020934XA patent/CN101490100B/en not_active Expired - Fee Related
- 2007-04-04 TW TW96112032A patent/TWI472542B/en not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001083672A (en) | 1999-09-08 | 2001-03-30 | Fuji Photo Film Co Ltd | Production of polymer and dye fixing element containing same |
WO2004026915A1 (en) | 2002-09-23 | 2004-04-01 | Ciba Specialty Chemicals Holding Inc. | Polymeric alkoxyamines prepared by atom transfer radical addition (atra) |
US20050250884A1 (en) * | 2002-09-23 | 2005-11-10 | Peter Nesvadba | Polymeric alkoyamines prepared by atom transfer radical addition (atra) |
WO2005116092A1 (en) | 2004-05-31 | 2005-12-08 | Sumitomo Seika Chemicals Co., Ltd. | Method for producing crosslinked poly(meth)acrylate compound |
Also Published As
Publication number | Publication date |
---|---|
EP2013240B1 (en) | 2017-05-31 |
TWI472542B (en) | 2015-02-11 |
WO2007115939A1 (en) | 2007-10-18 |
TW200745184A (en) | 2007-12-16 |
JP2009532544A (en) | 2009-09-10 |
CN101490100B (en) | 2012-08-22 |
JP5364947B2 (en) | 2013-12-11 |
CN101490100A (en) | 2009-07-22 |
US20100240858A1 (en) | 2010-09-23 |
EP2013240A1 (en) | 2009-01-14 |
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